Itinerary: Weekend Trip

By popular demand: My suggestions for what to do with your weekend in Portland.

I have been getting a lot of questions lately about what to do and see when visiting Portland.  There is a lot to do both in and out of town, but if you only have a couple days, how should you prioritize activities?  Here are my suggestions for a 3-Day weekend, arriving Thursday night and leaving Sunday afternoon.

west end ace hotel


5:00pm: Arrive in Town
Check in to a Hotel.  I don’t get to stay in local hotels often since I live here, but I have a few suggestions. If you are looking for luxury The Heathman Hotel (I am a brand ambassador and recently stayed the night, check out my experience here) is a classic option, or for something more modern The Nines is ideally located right next to Pioneer Courthouse Square in downtown.  Also downtown you will find The Ace Hotel, perfect for the young and hip, and the quirky Crystal Hotel.  As you might expect, Hiltons and Marriotts are scattered around also.  As a general guideline, stay within walking distance of West Burnside, a major artery that marks the line between the north and south sides of the city.

7:00 Dinner:
No need to travel far for food.  There are a lot of great restaurants and bars downtown, but on your first night, I suggest walking into the Pearl District and hitting one of the brewpubs: Deschutes, Rogue or Bridgeport are all great options.

9:00pm: Have some fun.
Wander to one of the nearby bars for some after dinner fun: Try a craft cocktail at the Teardrop Lounge or Multnomah Whiskey Library.  Play some billiards and catch a game at Henry’s Tavern or relax with an arthouse movie at the Living Room Theater, where they serve a full bar menu along with your popcorn.


Springwater corridor trail. Photo: KristiDoesPDX


9am: Breakfast.
If Voodoo Donuts is on your list of places to visit, this might be the time to brave the line.  Or if you need something more substantial, consider Tasty N Alder, Mother’s Bistro or the Byways Cafe for some excellent food.

10am: See the city!
I suggest renting a bike (or using the new Biketown bike share system) and touring our local neighborhoods.  Downtown and the Pearl District are great, but the neighborhoods are where life is happening.  I suggest a loop from downtown to Southeast Hawthorne and Mt. Tabor Park, then across town to Alberta Art’s District and finally to Mississippi Avenue.  You’ll find plenty of places to eat, drink and shop along the way.

If setting off on your own isn’t your style, try a Portland Walking Tour.  I’ve taken the Underground Tour, which is a lot of fun (although not as much “underground” as I was hoping), and I’ve heard great things about the Epicurean Excursion.  I also highly recommend a kayaking tour, it is beautiful!

Another option, especially if you have kids in tow, is to head to Washington Park for the Oregon Zoo, Children’s Museum, Rose Garden and Arboretum.  You can take the Max train from downtown. In the summer, bus 83 provides free transportation within the park.

I suggest heading over to SE Division Street, which is becoming Portland’s culinary district.  The famous Thai food spot, Pok Pok, is there, along more than a dozen other great restaurants.  Or just check out my list of “Where To Eat” for other ideas.


Beacon Rock Trail Photo: KristiDoesPDX


Get out of town!  If you are able, rent a car and head out of the city to do some exploring in the Columbia River Gorge.

8:00am: Breakfast:
Before you leave hit one Portland’s craft coffee shops to grab a drink and a bite for the road.  My favorite place is Ristretto Roasters, but Coava, Heart, Water Avenue and Barista are all great stops as well.  (Although pretty much every coffee shop serves a local roasts, so you really don’t HAVE to go out of your way for coffee).  After you’re caffeinated, head east on I-84.

9:00 am: Head to the Gorge
You will probably want to stop and see famous Multnomah Falls, but I suggest continuing on to one of the other dozen hikes nearby if you want to do a little hiking.  Latourelle Falls, Angel’s Rest or Horsetail Falls are good options. Please make sure you are prepared with maps, food, water and charged cell phone.  The trails are generally well marked but a surprising number of people get lost.

Lunch: Hood River
Keep driving east to the town of Hood River, a mecca for wind and kite surfers.  I suggest getting lunch at Double Mountian Brewery or Pfreim.  After lunch consider driving the “Fruit Loop,” a 30-mile loop that will take you to wineries, fruit stands, cider makers, weird museums and odd roadside attractions.  Or instead, cross the river into Washington and drive SR-14 for a quick hike up Beacon Rock before heading back to Portland.

Dinner: Back in Portland
I suggest going big.  Make reservations for Beast, Departure or Olympic Provisions, or brave the lines at Toro Bravo or Ox.  Toro Bravo remains my favorite restaurant in town, but the wait on weekends call be 2+ hours!  If you need ideas, check out for their ongoing list of  Essential Portland Resturants.

tasty n alder 1

Chocolate Doughnut at Tasty N’ Alder Photo: KristiDoesPDX


9am: Brunch.
Brunch is big here, but again, it can mean long lines.  A few suggestions are Tin Shed, Pine State Biscuits, Screen Door or Tasty N’ Sons.  Tin Shed is my favorite place because they give you potato pancakes instead of hashbrowns.  They also have a very veggie/vegan friendly menu and a special menu for dogs.  That’s right, you can bring your dog to breakfast.  #onlyinportland

Afternoon: Shopping or Walking 
How to spend your final hours in Portland?  If you haven’t been to Powell’s Books, go now!!! Or walk the waterfront loop. It’s a little less than 3-miles, the views from the East side are great, plus you probably need it to walk off all that food and beer!

 3:00PM: Leave Town
Hope you enjoyed the Rose City!

Well, that’s my suggestion for how to have an action-packed weekend in Portland.  But here are a couple alternatives:
– Instead of heading into the gorge, go to the coast.  It’s only an hour and a half to the cute ocean towns of Cannon Beach & Seaside.
– During the winter you might want to skip the gorge and head for Mt. Hood instead to ski, snowboard, snowshoe, sled or drink hot toddies in a lodge.
– Or if it’s raining (there’s a good chance of that any time of the year) stay in town and visit the Oregon Museum of Science and Industry or the Portland Art Museum.

Have a great time!  Let me know if you make any awesome discoveries of your own.



3 Comments on Itinerary: Weekend Trip

  1. This is a fantastic post – but I got halfway through it before I realized you were talking about Portland OR!! Not Portland ME! You come up on Google for Portland ME itineraries. Hopefully someday I’ll make it to the other Portland!

  2. Thank you so much for sharing your tips for a good Portland weekend. I’m planning a weekend in December. Would you have anything to add to the list considering the colder temps? Is there anything special going on for holiday season?

    I look forward to to hearing from the you!

  3. Thank you so much for this! Planning a girls’ long weekend trip to Portland, and I appreciate you sharing your itinerary!

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